Gossip Girl: The Next Generation
by Tasha9315
Summary: Nate/Serena, Chuck/Blair, Dan/Vanessa, Jenny/Andrew and Carter/Penelope are married with teenage kids. This fanfic focuses on their children and the drama in their children's high school lives. Nate Archibald/Serena van der Woodsen, Chuck Bass/Blair Waldorf, Dan Humphrey/Vanessa Abrams, Jenny Humphrey/OC.
1. Chapter 1

**My fanfic on Gossip Girl's next generation. Nate/Serena, Chuck/Blair, Jenny/Andrew and Carter/Penelope are married with teenage kids. Andrew, Jenny's husband is a new character that I created.**

**You can watch the opening credits and character promo on my Youtube channel (Tasha9313)**

watch?v=Wz7rZXgnd7g (Opening credits)

watch?v=vyg-E2kDoW8 (Character profile)

**But just in case, the families are as following:**

**Archibald children (Nate and Serena)**

Caitlin Serena Archibald (17 year old senior)

James Nathaniel Archibald (15 year old sophomore)

Cameron Howard Archibald (15 year old sophomore) (fraternal twin of James)

**Bass children (Chuck and Blair)**

Henry Bass (19 year old college freshman)

Zachary Bass (17 year old senior)

Audrey Bass (15 year old sophomore) (Have not decided on middle names for the Bass children)

**Humphrey children (Dan and Vanessa)**

Michelle Humphrey (17 year old senior)

Jonathan Humphrey (15 year old sophomore)

**Ritcher children (Andrew and Jenny)**

Samuel Ritcher (17 year old senior)

Isabella Ritcher (15 year old sophomore)

**Baizen children (Carter and Penelope)**

Sydney Baizen (17 year old senior)

Haley Baizen (15 year old sophomore)

Caleb Baizen (15 year old sophomore) (fraternal twin of Haley)

In 2017, St. Jude's and Constance Billard had been merged into a co-ed school called the Constance Jude Academy after both schools were bought by a new management.

**January 2033**

The Archibalds were having breakfast at the Archibald triplex penthouse with the three Archibald children dressed in their school uniforms.

"I'm going over to Jonathan's after school," James announced as Cameron cringed.

"Of all the boys in school to pick as your best friend," Cameron began as his brother glared at him from across the table.

"I could ask you the same thing. Of all the boys in school, Baizen's your best friend?" James fired back.

Nate and Serena glanced at each other uncomfortably. Aside from Cameron, the Archibalds were not fond of Caleb Baizen.

"Well, at least he comes from a family with a social standing unlike that Humphrey," Cameron shot back.

James stood up furiously and was about to leave the dining table, but was held back by his father.

"Calm down, James and sit," Nate sat him back down.

"Dad, you see how he speaks. It gets on my nerves," James said indignantly.

"Your brother has a point, Cameron. It's not right to insult someone based on their social status," Nate rebuked.

"I don't get why our family is friends with the Humphreys. Families like ours should only be friends with families from our social status, not people like the Humphreys," Cameron tried to appeal to his family.

"Who gave you that stupid advise? Caleb?" Caitlin asked sarcastically.

"He has a point," defended Cameron.

"Cameron, as we've repeatedly told you, having money and a social standing doesn't make a person superior," Serena exasperatedly tried to get through to her son.

"Sorry mom, but I don't believe that. People are born into different classes for a reason," said Cameron as the rest of the family looked at each other, shaking their exasperated heads in disbelief.

* * *

Students at Constance Jude Academy were lingering around, waiting for the bell to ring. As the Archibalds arrived, Caitilin left her brothers to walk over to a bunch of seniors including her best friends Michelle Humphrey and Zachary (Zach) Bass.

"Cam!," Caleb exclaimed as the two boys greeted each other. "James," he curtly acknowledged James who curtly acknowledged him back. His sister Haley was by his side, looking bashful.

"Hi Haley," James greeted her.

"Hi James," she replied, blushing furiously.

They then parted ways as Haley and Caleb headed to their respective classes. James and Cameron were to have the same Chemistry class together during first period.

"She's usually not that shy when you're not around," said Cameron.

"You mean she actually says more than two words when I'm not around?" asked James.

"Well, yeah! She's still shy, but not as shy when you're not around," replied Cameron.

"Maybe, she's just more comfortable around you since you're always over at her house, visiting Caleb," James reasoned as the fraternal twins entered the school building.

* * *

It was the period before lunch. James Archibald, Jonathan Humphrey, Audrey Bass and Haley Baizen were in Mrs. Baker's English class together.

"Class, for your assignments, I want you all to divide into pairs of two according the order of your names on the name list. For example, the first person on the list would be paired with the second person on the list; the third person on this list would be paired with the fourth person on this list and so forth. There are twenty four of you in this class," Mrs. Baker explained as she passed the list around the class. "Your partner would be the same for all the class assignments," Mrs. Baker added.

As Haley got hold of the list, her heart skipped a beat as it always did when she saw James. The names on the name list were in alphabetical order and the first 2 names on the list were Archibald, James Nathaniel and Baizen, Haley Elizabeth.

"I bet we're paired together since both our last names start with B," her best friend Audrey said as she took the list from her. "Ooh!" she exclaimed as she saw the list.

Audrey who was third on the list was well aware of Haley's crush on James and began playfully teasing her bestfriend about being paired with him.

"Cut it out," said Haley, indignantly.

"Your first assignment would be to select a well-known author from the ninteenth century, do a brief history on the author and interpret of one of the author's novels," Mrs. Baker instructed her sophomore class.

* * *

After the class was dismissed, James and Jonathan walked over to Haley and Audrey.

"Humphrey" Audrey sneered.

"Bass" Jonathan returned the sneer.

"Hey, since we're partners, I figured we should get started on our assignment this Friday. I mean, since it's due in two weeks," James said to Haley with the friendly smile he always gave her.

"Yeah...sure. Should we meet at my place?" asked Haley nervously.

She was blushing as she managed to string those words together.

"Ok, I'll be over at your place after school on Friday," said James.

"Why are you going over to her place, baby," came a bossy voice that belonged to James' girlfriend, Rachel Zielner. She had her two bestfriends with her as usual.

"Umm..., to work on our English assignment. Haley and I are partners in English class," answered James.

"Funny Jonathan and you aren't partners since you're best friends and everything," said Rachel with an uncomfortable laugh.

"Mrs. Baker paired the class up," James explained.

"Oh, ok," said Rachel, clearly not happy about the situation. But she decided to let it go. "James, let's go to for a movie after school. There's this new movie out that I can't miss," said Rachel, as she inserted her arm into his.

"Sorry Rach, but I'm studying with Jonathan after school. How about tomorrow?," asked James.

"Jonathan and you can study together tomorrow. I wanna see that movie today," she insisted.

"But I already promised Jonathan. How about you see it with your friends instead?, James suggested.

"I wanna see it with you," said Rachel with a threatening tone.

James looked uncertainly at Jonathan. Jonathan signaled understandably that he was fine with the change in plans.

"Alright, we'll go to that movie," James caved.

"Thanks! Carry my books," Rachel ordered as she put her books on his and dragged him away with her to the cafeteria, with her friends and Jonathan following behind.

"Maybe you could take this opportunity to get him to like you," Audrey suggested.

"But he has a girlfriend," said Haley.

"That Rachel? You saw how she bosses him around. Eventually he'll be tired of her being a total bitch and dump her," said Audrey a matter of factly.

"Well, even if that's true, I'm not gonna attempt to break them up. I'm not a boyfriend stealer," Haley replied.

"Okaay, if you insist on following the moral route. But if you change your mind, I could help you. We're family friends and I'm dating his brother so I could easily manipulate things your way" Audrey offered, true to being Blair's daughter.

"No thank you!," said Haley quickly as she and Audrey headed to the cafeteria.

Haley had always admired James and had a huge crush on him. They used to be friends, but as they grew into their teens, Haley's crush on James had made her to too shy to speak to him.

* * *

Dan and Vanessa were having lunch together at the Humphrey apartment.

"So, have Michelle and Chuck's son broken up yet?," asked Dan hopefully.

"You mean Henry? Nope, they're still going strong after two years," Vanessa answered as Dan groaned.

"Come on Dan, he's a good kid," Vanessa reasoned.

"Vanessa, he's Chuck and Blair's son. He could very well be pretending to be good because he has ulterior motives," Dan said cynically.

"Dan, one can't pretend for that long. Besides, we can't judge him by his parents," Vanessa reasoned.

"He's in college," Dan countered, knowing that he was quickly losing his argument.

"He's only a year older and Michelle herself would be in college next year," said Vanessa.

"Did I mention that he's Chuck and Blair's son?," said Dan, aware that he had already lost the argument.

"Oh, stop," Vanessa shook her head, grinning.

"Chances are, they'll last and we'll have to deal with Chuck and Blair as in laws won't we," Dan said dejectedly.

"I don't like that prospect either, but we're adults. We can be civil to each other as mature adults. If our daughter likes Henry, it's only right for us to be civil to Chuck and Blair for her," said Vanessa.

"You're right. But I'll only be civil if they're civil," Dan vowed. "I just hope he treats her right," he added as Vanessa squeezed his hand reassuringly.

**=to be continued=**

**A/N: Please remember to FOLLOW the story if you'd like updates and FAVORITE if you liked the story. **

**Please, please, review. I would really appreciate your opinions. Please let me know if you would like me to change anything about my style of writing. Thank you.**


	2. Chapter 2

A new school day was about to begin at Constance Jude Academy but as they usually did, the popular kids at Constance Jude hung out at the MET steps, sipping yogurt right before school. The school's Queen Bee, Sydney Baizen made her way up the MET steps with two of her minions as they joined the other minions including Audrey Bass, Isabella Ritcher (Jenny's daughter), Rachel Zielner and Haley Baizen who were sophomores. Haley wasn't a minion but had the freedom to sit with them due to be being Sydney's sister and Audrey's best friend. Sydney as the Queen Bee sat higher than the rest of the girls and the rest of the school kids.

As they were sipping their yogurts, Sydney spotted a quarto of seniors from her class, Sam Ritcher (Jenny's son), Caitlin Archibald, Zach Bass, and Michelle Humphrey at the bottom of the MET steps. Sam and Caitlin who had been dating for years were flirting with each other and holding hand. The Queen Bee rolled her eyes and tightened her lips.

"What does she have that I don't?" Sydney asked indignantly, crossing her arms.

"She's hotter and she's nicer," her minions answered in almost a whisper that they could barely be heard.

"What's that?" Sydey glared at them.

"We were saying, she's hot," said Audrey quickly.

"Well so am I," said Sydney vainly.

"You're hot, but Caitlin has the whole blonde, Barbie doll look," Isabella answered cautiously.

Sydney turned her attention to Isabella. "Sam's your brother, surely you can talk him into breaking up with Caitlin and sway him my way,"

"But, I don't have a problem with him dating Caitlin," Isabella protested.

"You have a problem with anything the Queen Bee has a problem with, if you want to stay in this circle," Sydney said threateningly.

"But, it's not like my brother would listen to me. He's in love with Caitlin and there's nothing I can say to change his mind," Isabella appealed.

"Well, start thinking. And find a weak point in their relationship," Sydney ordered.

"Yes, Sydney," Isabella complied.

Isabella loved her brother and liked Caitlin but staying in the Queen Bee's circle was important to her. She was even hoping for Sydney's favor in making her the next Queen Bee after Sydney graduated from Constance Jude.

Sydney and her minions got up to make their way to school. As they passed Sam, Caitlin, Zach and Michelle, Sydney walked up to Sam and greeted him with the flirty tone that she always used on him while she greeted Caitlin, Zach and Michelle with her usual sarcasm. She flirted in an almost subtle manner with Sam who answered her with a combined friendliness and awkwardness. Caitlin rolled her eyes but said nothing.

After Sydney and her minions walked away, Sam and Zach walked ahead of Caitlin and Michelle as the quarto headed to school.

"You're just gonna let her flirt that way with Sam?" Michelle asked Caitlin.

"Sam and I talked about it and came to an understanding that we love each other and are secure enough in our relationship to not be threatened by Sydney's inappropriate flirting," said Caitlin casually.

"Still, wouldn't it be better if you made Sam tell her to stop? If he doesn't say anything, she'd take it as him encouraging her flirting," said Michelle.

"Her flirting is usually kind of subtle that if someone called her out on it, she could easily deny it and dismiss being flirty as her nature," said Caitlin.

"She only flirts that way with Sam," Michelle pointed out.

"But there's no solid proof of that. She could easily twist things. Besides, I trust Sam, so it doesn't matter what Sydney says or does. Isn't trust the most important thing?" Caitlin asked.

"I guess you're right. Just like I trust Henry who's away at Columbia with all those college girls and who I only get to see twice a month," Michelle said longingly, reminiscing about her boyfriend with a smile.

"Yeah!" Caitlin agreed with a laugh.

Michelle's boyfriend, Henry Bass was the son of Chuck and Blair and the brother or Zach and Audrey.

* * *

Cameron Archibald had just shut his school locker when he felt the palms of his girlfriend, Audrey Bass over his eyes.

"Hey!" she greeted him.

"Hey babes!" Cameron greeted her as they kissed.

"I don't wanna spoil tomorrow's surprise but meet me at the HINGE Country Club at 7.30" Audrey said excitedly.

"Huh?" asked a confused Cameron.

"Our anniversary! It's tomorrow. I planned a surprise for us. Surely you kept our anniversary day free?," asked Audrey.

"Oh. Right," said Cameron trying to hide his confusion.

"You forgot our anniversary didn't you?," Audrey asked, disappointed.

"I ... umm ... I'm sorry. I forgot," Cameron admitted.

"I planned a candlelight dinner at the country club tomorrow evening," Audrey pouted .

"I'm sorry Audrey. Caleb and I already have a card game planned. We planned it weeks ago. We can celebrate next weekend," said Cameron.

"It's more important for you go to your stupid card game that you can reschedule than to celebrate our anniversary? Next weekend is no longer our anniversary," Audrey glared at him.

"I suppose I could reschedule the card game," said Cameron.

"Good," said Audrey as she walked away, still annoyed.

* * *

James Archibald and Haley Baizen were in the Baizen library at the Baizen penthouse, working on their English class assignment.

"Ok, first we have to pick an author from the ninteenth century," said James.

"Right," said Haley as she still struggled to speak to James without being shy or stammering.

"You know, you could say more than two words in front of me. I don't bite," said James with a friendly smile that made her melt.

Haley knew she had to get over her bashfulness in front of James if they were going to work together. Everything about James from his smile to his dreamy blue eyes to his personality had that effect on her that made her nervous and shy.

"Sorry about that. Sometimes,, I can be a little shy. As you were saying, we have to pick an author," said Haley doing her best to sound as normal as she could.

"Charles Dickens!" they both said together. They stared at each other slack-jawed for a moment.

"You like Charles Dickens?" James asked.

"He's my favorite author of all time," said Haley with a hint of sheepishness still in her tone.

"No way! He's my favorite too" said James, impressed.

"Really!" said Haley excitedly, but toned down her excitement as quickly as she could.

"Most people say I'm old fashioned and left behind in time for preferring classics, especially my brother," said James.

"My brother and sister tell me the same thing. Most people don't appreciate the beauty of classics," said Haley.

"Absolutely!," James agreed.

For the first time in ages, Haley was starting to feel relaxed around James as they engaged in a conversation about classics and Charles Dickens. They even had the same favorite book, David Copperfield which they chose as the book they would highlight in their assignment. Their laptops were used to search for the detailed information they needed for their assignment.

* * *

After James left, Sydney gave Haley a teasing look.

"Mom, Haley's in love with James," Sydney teased.

"I am not," Haley said defensively.

"Well, he is a looker like his father," said Penelope, impressed.

"Mom," Haley protested.

"There's nothing wrong with it," said Sydney.

"Except that he has a girlfriend. Rachel,"

"You mean that Isabella's daughter. That Isabella always competed with me and now her daughter's doing it with my daughter," said Penelope indignantly.

"It's not a competition. James and I are just friends who are working on our assignment together," said Haley.

"Life is a competition. I haven't given up on Sam Ritcher just because he has a girlfriend," said Sydney.

"It's not right for you to scheming against Sam and Caitlin that way," Haley crossed her arms.

"What's right to me is for me to get what I wand at any cost," said Sydney.

"Can't you respect the fact that they're together, move on and try to look at Sam as just a friend?" asked Haley.

"You mean like you're attempting to do with James. No way. When I want something, I have to have it," said Sydney pompously.

"Fine. But you're not going to succeed. They love each other and I'm sure there's no weak point for you to split them up," said Haley as she walked away annoyed.

"Your sister has a point. If your plan succeeds, that's fine. But if you fail, you'll end up humiliating yourself," said Penelope.

"Don't worry mom. I always win," said Sydney confidently with a calculating look.

**=to be continued=**

**A/N: Please remember to FOLLOW the story if you want updates and FAVORITE if you like it. And please REVIEW and tell me what you think about the chapter. Should I change my writing or dialogue style. Or should I change the storyline. Are 13 kids too confusing to remember? I have reduced the roles of some of them. I will post the 3rd chapter next week.**

**P.S. The Isabella that Penelope talks about is one of Blair's old minions from the show. I forgot this when I named Jenny's daughter the same name. Blair's old minion and Jenny's daughter are 2 different characters with the same name. Blair's minion is not even important to this story. I just wanted to give Penelope that line.**


	3. Chapter 3

Samuel (Sam) and Caitlin were making out in Sam's room at the Ritcher's triplex penthouse. They were planning on losing their virginities that day, but Caitlin who had second thoughts pulled away.

"What's wrong Caity?" her boyfriend asked apprehensively.

"Sam, I'm really sorry, but I don't think I'm ready," she said apologetically.

"But I don't understand. We planned this, weeks ago," he eyed her with confusion.

"I know. I'm sorry. I thought I was ready but I'm not." Caitlin looked down, unwilling to look into his eyes.

Sam ran his hands through his hair. "Is it me you're not sure about?" I mean, we've been dating for years, so we're not exactly rushing into this."

"No. Sam. I love you and I'm sure you're the one I want to lose my virginity to," Caitlin caressed his cheek. "I just feel this is a big step. We're still in high school, so I feel there's no rush or hard and fast rule that we have to get it over with by a certain time-frame."

"I'm sorry Sam. But I hope you understand," she said remorsefully.

Sam looked into Caitlin's eyes that were shining with tears and were probably sad because she felt bad about disappointing him. As disappointed as he was, he couldn't take that look on her eyes. He didn't want her to feel bad. And he knew it was not right for him to push her into doing something she wasn't ready for.

Doing his best to hide his disappointment, he wiped her eyes, took her hands in his and said, "It's alright Caity. I understand. I don't think I'm ready either".

"Thanks for understanding, Sam," she said gratefully as she hugged him.

He felt a jolt in his stomach. Physical contact was not making this easier. "No problem," he said, awkwardly.

Unbeknownst to them, Sam's sister, Isabella who was eavesdropping outside the room's door, heard the whole conversation.

* * *

"So, did you two actually manage to have a discussion with Haley being unable to keep her bashfulness under control in front of you," asked Cameron as James walked in the Archibald's penthouse.

Both brothers were still in their school uniforms, but their ties were loosened, their blazers were off and hanging on their arms and Cameron's shirt was tucked out.

"She was shy at first, but I told her I didn't bite. When we figured out that we both had the same favorite author and book, we actually had a normal, friendly conversation. It was actually really nice," said James.

"You mean David Copperfield?" Cameron scoffed.

"Yup," James said, with an inner pride that he couldn't explain.

"Great. So there's actually someone else who likes boring books from centuries ago," Cameron sniggered.

James rolled his eyes indignantly.

"So, it was really nice speaking to Haley, huh? Sounds like someone has a little crush on Haley" Cameron teased as James blushed.

"I do not. I like her as a friend. Besides, I'm with Rachel," said James defensively.

"Okaay," Cameron said sarcastically. "But she seems better than that bossy witch you call a girlfriend. Speaking of which, how do you deal with her? Audrey's starting to turn into one".

"What do you mean?" asked James.

"She got mad that I forgot about our anniversary and had a card game planned with Caleb that night," said Cameron casually.

"Well, of course she'd be mad if you forgot your anniversary," James said a matter-of-factly.

"I know, but I apologized and asked to postpone our anniversary date to next weekend. She got mad and insisted I cancel my already planned card game. I had to cave," Cameron shook his head in disbelief. "I don't see what the difference is if we celebrate our anniversary next weekend. It's still celebrating."

"The difference is, the weekend is no longer your anniversary. It's not the same as celebrating on the actual day. If something important came up, it's fine to postpone, but your card game can easily be postponed. It would come off to her as your card game was more important than your relationship," his brother advised.

"Girls are too analytical," said Cameron as Caitlin entered the penthouse.

"What's wrong sis?" asked James

"What? Nothing. What makes you think something's wrong?" asked Caitlin uncomfortably.

"Well, you look upset," James pointed out.

"You were at Sam's weren't you? Did he hurt you?" Cameron clenched his fist.

"Noo. Boys, I'm fine. There's nothing wrong, I promise," said Caitlin defensively.

"Okay," said James and Cameron together as they glanced at each other with narrowed eyes.

* * *

Sydney was laying on her bed in her room, on the phone with Isabella.

"Do you have any scoop for me yet?" she asked.

"I think I may have something," said Isabella.

"Well, let's have it," Sydney coaxed.

"I eavesdropped on my brother and Caitlin when they were about to do it," Isabella began as Sydney crinkled her nose and curled her lips.

"But Caitlin changed her mind and said she wasn't ready. Sam said he understood but I can tell he was disappointed," said Isabella as she launched into telling Sydney the details of the conversation she eavesdropped on.

"Hmm!" Sydney pondered on this. "Are you sure he was disappointed?"

"I'm pretty sure. I know how my brother acts when he's disappointed or tries to hide his disappointment," said Isabella.

"Oooh, this is just what I need," said Sydney triumphantly. "His guards are already weakened. I just need you to do one thing before I make my move," said Sydney.

"Sydney, this is my brother we're talking about. You talking about making your move on him makes me feel uncomfortable," said Isabella.

"Oh, don't be over-dramatic. Just do this one thing," she ordered as she gave Isabella her task.

**=to be continued=**

**Please let me know what you think about this chapter. Thank you!**


	4. Chapter 4

Samuel Ritcher was working on one of his school assignments on his laptop when he heard a knock on the door.

"Come in"

"Hey," came his sister, Isabella's voice.

"Hey,"

"Are you alright?"

"Why wouldn't I be?" asked Samuel, confused.

Isabella hesitantly looked at her brother. They didn't resemble each other much. Sam was a brunette and more closely resembled their father, Andrew, while Isabella was blonde and more closely resembled their mother, Jenny. She began feeling twinges of guilt. She convinced herself that Sydney genuinely loved Sam and didn't intend on hurting him. She needed to do this to stay in Sydney's in-crowd and be crowned Queen Bee once Sydney graduated. She shoved any bouts of conscience she had and went ahead with Sydney's assignment.

"Okay, don't freak, but I might have overheard Caitlin and you," Isabella began cautiously.

"You whaat? You mean you eavesdropped on me and my girlfriend," Sam said indignantly.

"I wasn't eavesdropping. I swear," Isabella said defensively. "I came to your room for something and I happened to overhear you."

"Yeah well, that was nothing," said Sam, dismissively.

"It wasn't nothing. Losing your virgi…"

"Izzie, I'm sorry, but you're my sister and I'm not comfortable discussing that with you. That was between me and Caitlin," said Samuel.

"That's not … I mean, I'm worried about your relationship in general, because Caitlin doesn't seem to love you as much as you love her," said Isabella.

"What are you talking about? Of course she loves me," said Sam.

"I don't know, Sam. If she loved you, why wasn't she ready?" asked Isabella, eyeing her brother's reactions closely.

"What does love have to do with being ready?" asked Sam.

"Sam, as a girl, I know how the female psychology works. Most of the girls in your grade have lost their virginities. Half of them to guys they weren't even in love with, and yet Caitlin who's supposed to be in love with you ….?" Isabella dragged her last point.

"What's that supposed to mean?" Sam crossed his arms.

"That it's not losing her virginity that she has doubts about. It's losing it to you," said Isabella.

"You're wrong. Caitlin told me herself it wasn't the case," said Sam defensively.

Isabella was pleased to sense a hint of denial in Sam's voice.

"You've both been together for years and you'll both be turning eighteen in a few months, and she's not ready even if she's apparently in love with you? Does that make sense if you consider the attitudes of the other girls at our school?" Isabella pressed on.

She searched her brother's face carefully. To her delight, he looked nervous and worried.

"Look, Sam. I have no reason to make this up. I don't intend to interfere in your love life, but I just want you to be careful because you're my brother and I love you. I don't want you to get hurt if Caitlin doesn't feel as strongly about you as you do about her," said Isabella with fake concern.

Judging by the look on Sam's face, she knew that she had successfully planted the seeds of doubt in his mind.

"Just think about what I said and be careful. If Caitlin doesn't feel the same way about, you, it might be best to move on to someone who actually returns your feelings," said Isabella.

She kissed him on the cheek and walked away with a satisfied smirk, leaving him to his thoughts. Phase one was complete.

* * *

That Saturday morning, James and Haley entered the Archibald library to work on their English assignment.

"Nice library," said Haley, taking in the beautiful marble flooring, panel walls, furniture and racks.

"Cameron and your brother love spending time here," said James.

"Yeah right," said Haley, disbelievingly.

"It's true. Napping on the extra-comfy couches happens to be one of their favorite pastimes," said James as they both sniggered.

They were browsing through books for their assignment when Haley looked around at the other inviting books at the library.

"You can have a look around and check out the other books if you like," said James courteously.

"Thanks!"

Haley browsed through a section that contained law books. She picked one up and flipped through the pages.

"Great law book collection," said Haley.

"Courtesy of my dad," James shrugged.

"Planning on going to law school like your dad?"

This question escaped Haley's mouth without her even thinking. She inwardly cursed her tactlessness. She had asked him a question that was too personal as if they were buddies. To her relief, he didn't seem to mind.

"Maybe, but I think I prefer specializing in Criminal Law instead of Family Law," James shrugged.

"That's great!" said Haley.

James and Haley launched into a conversation about the laws they disagreed with.

"So, what do you plan on doing in college?" asked James.

"I haven't decided on my Pre-Med yet, but I plan on going to Medical school and specializing in Pediatrics," said Haley.

"Cool! My Grandpa Will's a doctor too," said James impressed.

As James and Haley sat down working on their assignment, Haley couldn't help but steal a lingering look at James. It was gradually becoming easier for her to be around him but she wasn't sure if it was good thing as she liked spending time with him and talking to him. She hoped this meant she was gradually coming to view him as a friend, but she was afraid her attraction was turning into something deeper as she got to know him. She couldn't tell the difference, but she knew he still had that effect on her where he made her heart flutter. She constantly told herself to suppress those feelings as he had a girlfriend, but it would take time to completely get over the feelings that she harbored for him years.

* * *

Cameron Archibald and Audrey Bass were having dinner at the HINGE Club.

"How's the food?" asked Audrey.

"Excellent. You have good taste, Auds," said Cameron, impressed.

Audrey smiled at the complement and reached across the table to put her hand on his. Cameron returned the smile and put his other hand on hers. For a few moments, they gazed at each other with their palms clasped together. But alas, the moment didn't last, as Cameron's cellphone rang. Audrey rolled her eyes at the sight of Caleb's picture on his screen. It was the third time that Caleb had called in the past hour and each time, Cameron had no qualms about giving Caleb his full attention.

"Sorry Auds," said Cameron as he answered his cellphone.

"Caleb, what's up," he said, enthusiastically.

Each time Cameron answered Caleb's call, he answered with more enthusiasm than the last and it was beginning to wear Audrey out.

"Oh man. No way. I can't believe I missed it," said Cameron, disappointedly as Audrey began tapping her fingers on the table.

Caleb was at the card game that Cameron missed for their anniversary dinner. After about fifteen minutes, he finally put his phone down and was in a sulky mood throughout dinner.

"What's wrong?" Audrey asked impatiently.

"I missed the best card game of the decade. They played a more interesting card game and there were new stakes," Cameron crossed his arms, pouting.

"Cam, why don't you go to your stupid card game alright? You don't have to torture yourself spending the evening with me. I'm done," Audrey stood up with her hands in the air.

"Done with dinner?" asked Cameron.

"Done with RELATIONSHIP," said Audrey abrasively.

"You're breaking up with me?" asked Cameron disbelievingly.

"That's right. We're over," said Audrey dismissively.

"But Auds…What did I do?" Cameron implored.

"You spent most of the evening on the phone with Caleb and complaining about missing a 'great' card game. Go ahead to Caleb and your card game which are clearly more important than me and our relationship," said Audrey bitingly.

"Auds, I'm sorry. I promise, no more complaining," said Cameron.

"Forget it. It's not just about today. You hardly ever show an interest in our relationship and your endeavors with Caleb have always been more important to you. This is the last straw," said Audrey with defeat in her voice.

"Auds ..." Cameron began.

"Goodbye, Cameron," Audrey said before storming off.

"Auds … Audrey … Come back," Cameron begged but Audrey stood by her decision.

Cameron watched hopelessly as she walked away.

**A/N: Please, please review, so that I know if I need to improve or change anything. One thing I need to apologize for is if I come off as using tell instead of show in areas when I'm supposed to used show instead of tell. The "show not tell" is something I'm definitely working on.**

**For those of you who were waiting for Chuck and Blair, they appear next chapter. There would both an Archibald family moment and a Bass family moment next chapter. And also a Humphrey family moment too, but that would involve Henry Bass.**

**I haven't decided if I want Audrey to eventually get back together with a reformed Cameron, or if I want her to move on to Jonathan Humphrey. Which would you prefer?**


	5. Chapter 5

**A/N: I am sooo sorry that I haven't updated in a very long time. **

Dan and Vanessa were seated across from Henry and Michelle at a fancy restaurant. He eyed the young boy who had stolen his daughter's heart with narrowed eyes. It was like looking at Chuck from twenty years ago. Aside from their facial resemblance, Henry was also an elegant dresser like his father. Dan could tell his outfit was branded from head to toe.

"What are you planning to major in, Cameron?" asked Vanessa.

"In Business, Mrs. Humphrey. I plan on taking over Bass Industries when my father steps down," said Henry with a charming smile.

Dan rolled his eyes. This kid was clearly planning to be a Chuck Bass 2.0.

"So Cameron … why Michelle? I mean, she's still in high school, you're in college. You're a Bass, she's a Humphrey," asked Dan as Vanessa nudged him and gave him a warning look. '

"I love Michelle for the wonderful person that she is, Mr. Humphrey. It doesn't matter to me what her last name is", said Henry as Michelle and Vanessa looked at him with awe.

But unlike his wife and daughter, Dan wasn't immediately buying what he considered a clever act. This was going to be a long night.

* * *

Cameron Archibald returned to the Archibald Triplex penthouse to find the rest of his family having a chat in the hall. The family butler had taken his coat, so he threw his tie on the couch and slumped on it, in a huffy mood.

"What's wrong Cam?" asked Serena.

Cameron looked the curious and slightly worried looks of his family. His parents were still attractive in their early forties, something that often gained compliments from his friends. Caitlin mostly resembled Serena, with blonde hair and blue eyes. James was a brunette and mostly resembled Nate except for his eyes which were blue like Serena's. Cameron was also a brunette like his father and brother but was a good mix of both his parents in looks.

"Audrey broke up with me," said Cameron, clasping his hands over his head.

Serena gasped, Caitlin had her hands over her mouth, James dropped the pillow in his hand and Nate stared at him with his eyes wide. No one close to Cameron and Audrey would have expected the couple who had been together since the fifth grade to break up. They had been so perfect together. Cameron himself thought they were nothing less than perfect and was in complete shock.

"What? Why?" asked Serena who was the first to recover.

Cameron narrated the story of how Audrey broke up with him as his family listened intently.

"Darling, I think Audrey just feels you don't prioritize her. I'm sure she didn't mean it and would take you back if you showed her how important she is to you," said Serena encouragingly.

"Am I not allowed to have a life outside of her?" asked Cameron indignantly.

"No, but it's not too much for her to ask for your undivided attention on your anniversary," said Nate.

"So what do I do to get her to take me back?" asked Cameron.

"For starters, you could apologize and tell her how wrong you were for not prioritizing her on your anniversary," his older sister suggested.

"And you could promise not to repeat it again," his twin brother added.

Cameron rolled his eyes. "Fine, I'll try," he resigned, getting up from his seat and heading for his room. He was soon followed by his siblings.

Serena looked apprehensively at Nate. "I don't know how to get Cameron to realize his faults" she said as Nate nodded understandingly and took her hand in his.

"We tried advising him many times. All that's left is for him to learn from experience. Maybe losing Audrey would be the wake-up he needs", Nate shrugged.

"I hope so. But poor Blaire would be the most disappointed. She was really hoping we'd become in laws," said Serena.

"Maybe they'd get back together," said Nate.

"I hope so," Serena said, laying her head on Nate's shoulders as he put his arm around her and kissed her temple.

* * *

"You broke up with Cameron?" asked Blair alarmed.

Audrey sighed at the apprehensive and shocked expressions of her parents and brothers. Henry was home for the weekend and had just gotten back from dinner with the Humphreys.

"Mom, his friends have always been more important to him that me. And today he proved poker was also more important than me," said an upset Audrey who went on to explain what had transpired during their anniversary dinner.

"Auds, teenage boys are stupid that way. We have to mould them and guide them," said Blair. "I meant most teen boys, not all of them," she quickly amended at the stares from her sons.

"I tried. He won't change. I'm done trying," Audrey's arms were crossed as she shook her head.

"But …" Blaire began.

"Mom, please. I'm done discussing this. Nothing you say is going to change my mind," said Audrey as she stood up and began walking away towards the stairs.

"Audrey, wait", Blaire got up from her seat and walked behind her daughter who continued on her path. "Audrey. AUDREY," but Blaire's protest was ignored as the teen had reached up the stairs.

"I'm sure they'll work things out eventually," said Chuck, who had stood up and put his arms around Blaire while sitting her back down.

"Henry, how did dinner with the Humphrey's go?" asked Chuck.

"To be honest, I'm positive Mr. Humphrey hates me," said Henry.

"You'd think that with all Humphrey's self-righteous virtue-signalling, he'd be decent enough not to project his hate for me onto my son. Would you like me to have a word with him?" asked Chuck.

Henry seemed to be contemplating this, but Blaire objected with a resound "Noo".

"Why not?" asked Chuck.

"With the history between you two, I'd be surprised if at least one of you wouldn't end up in the hospital," Blaire shook her head. "Henry, this is why I said Humphrey's daughter is a bad choice. Your father and I can't be in the same room as Dan and Vanessa".

"Can't you guys be civil for your children? Aren't you all adults?" asked Henry indignantly.

"How set are you on Humphrey's daughter?" asked Chuck.

Henry looked at the hopeful looks of both his parents. "I love her. So I'm pretty set," he crossed his arms as Chuck and Blaire exchanged apprehensive looks.

"How about both your mother and I have a meeting with Dan and Vanessa," Chuck suggested.

"Chuck, Vanessa and I can't stand each other either," said Blaire.

"But we can do it for our son's happiness can't we? If Humphrey and Vanessa cared about their daughter, they'd agree to do the same".

"Fine, we can try," Blaire relented. "If you'll excuse me, I have to go call Serena" she said, giving Chuck a peck on his cheeks before she rose from her seat and headed upstairs.

"Dad, what if mom is too preoccupied with Audrey's relationship that she forgets what she said about meeting Michelle's parents?"

"Don't worry. Your mom has an excellent memory power. Trust me, I should know. If she forgets, I'll remind her. I promise," Chuck patted his son reassuringly as Henry nodded with a small smile.

**=to be continued=**

**Please review**


	6. Chapter 6

**I apologize that I haven't updated in a while. I promise to update more often. **

Cameron's recent break-up with Audrey added to his Monday morning gloom. He had called her and texted her about a hundred times, but she had only replied to one his texts, telling him to leave her alone.

"She'll come around. Even if she doesn't, there are plenty of fish in the sea," said Caleb as Cameron scowled.

"Audrey, wait." Cameron followed her to her locker.

"Cameron, I told you we're over and to leave me alone," Audrey crossed her arms.

"Audrey, I'm sorry. I promise, I'll prioritize you more. Please give me another chance," he pleaded.

"Oh my goodness. I'm done discussing this. I've given you plenty of chances," she said exasperatedly.

"Please. I'll do anything"

"Okay. Then do one thing. Stop being friends with Caleb."

"That's not fair. He's my best friend. I don't tell you to stop being friends with your best friend," said Cameron indignantly.

"Fine, be friends with Caleb. But forget me," said Audrey as she walked away.

"Audrey ... Audrey" Cameron slammed the locker next to him as Audrey looked back, shaking her head.

Caleb put his arm on his shoulder. "I told you man. Not point forcing her. If she doesn't want you, forget about her. There are plenty of other girls. You're finally free to explore instead of being stuck with the same person since fifth grade".

"But …"

"If you really want her, maybe she'll come around once she's cooled down. But for now, let's get to class. Come on." Caleb ushered Cameron away from the lockers.

* * *

Sydney tapped her feet and fidgeted with her hair as she sat on the bench outside the school counselor, 's office. She had half a mind to barge in and complain about how long it was taking when the door opened and Caitlin came out.

"Ms. Baizen, you're next," said Mrs. Figgs.

Both girls rolled their eyes at each other before Sydney entered the office.

"Brown and Columbia? But I applied to Yale," she said indignantly as she eyed Brown and Columbia's brochures on the desk.

"My apologies, Ms. Baizen. Those were Ms. Archibald's. I'll just put those away and get the Yale Brochure."

"I thought she applied to Columbia?" asked Sydney.

"Columbia and Brown. She's confused about where to attend."

Sydney perked up with interest. "Has she decided?"

Mrs. Biggs ran her hands through her hair and adjusted the cuffs of her sleeves. "Ms. Baizen, I'm not at liberty to discuss that. I've already told you too much."

"But just enough for me to stir up trouble," Sydney thought to herself.

* * *

Sydney exasperatedly rolled eyes at a bunch of loud students that she passed as she made her way through the cafeteria. She spotted Caitlin and her friends. Despite what Isabella said about Sam's disappointment, he showed no signs of being any less interested in Caitlin. The couple looked just as happy as they usually were.

"Caitlin, it was nice bumping into you outside 's office. It's a bummer that you're confused between Brown and Columbia. I hope you manage to figure it out," said Sydney with tones of mock concern.

Sam narrowed his eyes "Wait what? You applied to Brown?"

"I was going to tell you. But I didn't know how," Caitlin said quickly.

"But we always planned on going to Columbia together," said Sam.

"I know. But I'm confused if I want my whole life to be in New York or I should at least explore college life in a different state. And Brown has been part of my family's history."

"Why didn't you tell me?" he asked indignantly.

Caitlin blushed as she looked down. "I'm sorry. I wanted to. But you were all excited about us being at Columbia together and I was afraid."

"Have you decided?"

"I'm still confused."

"If you'll all excuse me. I need to get some air," said Sam as he walked away, ignoring Caitlin weakly call after him.

Sydney walked away feeling triumphant. All she would need now is to get Isabella to use this to further plant doubts in Sam's mind about Caitlin's feelings for him.

* * *

Audrey has to control herself from yawning as Mr. Drummond, her History teacher drawled on in front on the class.

"Alright class, I expect a detailed report on Christopher Columbus and you'll be working in assigned pairs," Mr. Drummond announced.

Audrey groaned. She hated assigned pairs. She always ended up being assigned with someone she couldn't stand.

"Smith, you're to pair with Wilson, Davis, you're to pair with Calhoun, Bass, you're to pair with Humphrey …"

Audrey just knew it. She looked at Jonathan who looked just as annoyed as her. At least they agreed on something.

"But Mr. Drummond, Humphrey and I don't get along. It would interfere in the quality of our work. Please switch our pairs," she tried to reason.

"I'm sorry, Ms. Bass. I'm afraid I can't do that. Working with someone you don't get along with is character building and prepares you for the workplace where you can't object to working with someone you don't get along with," he said.

Audrey cornered Jonathan after class. If they were stuck working together, she had to make the best of it.

"Listen Humprhey. I don't like working with you …"

"And working with you was just on top of my wish list," said Jonathan.

"Bup, bup … I am still talking," Audrey held up her hand. "I'm not going to let you ruin my grade. We'll just have suck it up and work on this assignment in a civil manner before going back to hating each other. Do you have a problem with that?"

"Fine by me," he said.

"Good" she said before walking away, with her nose up in the air.

**=to be continued=**

** Please, please review**


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